Acetone → ACH-806

HRID 901891Notes

Reaction equation

HRID 901891 reaction equation
[S-:1][C:2]#[N:3].[NH4+].Cl.[CH2:6](Cl)[C:7]1[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=1.[CH2:14]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][C:21]=1[C:27]([F:30])([F:29])[F:28])[CH2:15][CH2:16][CH2:17][CH3:18].CC(C)=[O:33]>C(Cl)Cl>[CH2:14]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:2]([NH:3][C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[O:33])=[S:1])=[CH:22][C:21]=1[C:27]([F:28])([F:29])[F:30])[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 180Acetone2×HCID 15666Ammonium thiocyanateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 176055714-(Pentyloxy)-3-(trifluoromethyl)aniline

Product 1

HCID 11640186ACH-806

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ammonium thiocyanate (4.5 g, 60 mmol) in acetone (25 ml) is added to a suspension of nicotinyl chloride hydrochloride (3.6 g, 20 mmol) in acetone (50 ml). The reaction is stirred for 1 h at room temperature followed by the addition of a solution of 4-pentyloxy-3-trifluoromethyl aniline (4.9 g, 20 mmol) in methylene chloride (25 ml). Stirring is continued over night at room temperature. The solvent is evaporated and the residue suspended in water (100 ml) and extracted with ethylacetate (3×75 ml). The organic extract is washed successively with 10% aq. NaHCO3 solution (×1), water, and brine. The organic layer is dried over sodium sulphate and evaporated. The residue is crystallized from methanol to give the desired product 1H NMR (300 MHz, CDCl3): δ 12.34 (s, 1H), 9.35 (s, 1H), 9.16 (s, 1H), 8.91-8.88 (d, 1H, J=6.4 Hz), 8.23-8.20 (t, 1H, J=2.2 Hz), 7.85-7.81 (d, 1H, J=12 Hz), 7.54-7.50 (q, 2H, J=4.8 Hz), 7.04 (d, 1H, J=8.7, 1.0 Hz), 4.10-4.06 (t, 2H, J=6.3 Hz), 1.92-1.83 (m, 2H), 1.50-1.42 (m, 4H), 0.97-0.93 (m, 3H). MS (APCI) m/z 412.14 [M+H]+.

Workup

  1. stirringStirring
  2. waitis continued over night at room temperature
  3. customThe solvent is evaporated
  4. extractionextracted with ethylacetate (3×75 ml)
  5. extractionThe organic extract
  6. washis washed successively with 10% aq. NaHCO3 solution (×1), water, and brine
  7. dry with materialThe organic layer is dried over sodium sulphate
  8. customevaporated
  9. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-0bcad7af3f244c638ea20558e127265a
Source dataset
uspto-grants-2008_04
Patent number
US07365068B2

Reaction notes

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